Triethylamine → 4-[4-(3-Methanesulfonyl-benzylamino)-5-trifluoromethyl-pyrimidin-2-ylamino]-1,3-dihydro-indol-2-one

HRID 857438Notes

Reaction equation

HRID 857438 reaction equation
C(O)(=O)C.[CH3:5][S:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][NH2:13])(=[O:8])=[O:7].Cl[C:18]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][N:21]=[C:20]([NH:28][C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH2:31][C:32](=[O:38])[NH:33]3)[N:19]=1.CCN(CC)CC>O1CCOCC1>[CH3:5][S:6]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH2:12][NH:13][C:22]1[C:23]([C:24]([F:25])([F:26])[F:27])=[CH:18][N:19]=[C:20]([NH:28][C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH2:31][C:32](=[O:38])[NH:33]3)[N:21]=1)(=[O:7])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 218684954-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-1,3-dihydro-indol-2-oneHCID 860811393-Methanesulfonyl-benzylamine mono-acetate

Product 1

HCID 116701324-[4-(3-Methanesulfonyl-benzylamino)-5-trifluoromethyl-pyrimidin-2-ylamino]-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-methanesulfonyl-benzylamine mono-acetate (150 mg, 0.61 mmol) and 4-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-1,3-dihydro-indol-2-one (200 mg, 1 eq) were combined with Et3N (136 mg, 2.2 eq) in dioxane (3 mL) at 100° C. for 3 hours. The reaction was cooled to RT and product crystallized by the addition of water to the crude reaction. The product was filtered of as a tan solid, 139 mg (48%). 1H NMR (DMSO-d6, 400 MHz) δ 3.11 (s, 3H), 3.39 (s, 2H), 4.62 (d, J=5.8 Hz, 2H), 6.48 (d, J=7.5 Hz, 1H), 6.96 (m, 1H), 7.07 (d, J=8.3 Hz, 1H), 7.53 (m, 2H), 7.75 (d, J=7.5 Hz, 1H), 7.83 (m, 2H), 8.19 (s, 1H), 9.08 (s, 1H), 10.31 (s, 1H); HPLC ret. time: 5.314 min. LRMS (M+) 478.2.

Workup

  1. customproduct crystallized by the addition of water to the crude
  2. customreaction
  3. filtrationThe product was filtered of as a tan solid, 139 mg (48%)

Sources & evidence

ORD record
ord-e55ecd02793149eebd6a764702bf1f40
Source dataset
uspto-grants-2006_12
Patent number
US07145008B2

Reaction notes

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